Prison of Regrets
by music-and-fairytales
Summary: Underworld fic! Emma goes to the Underworld to rescue Killian, but finds a strange and dark enchantment keeping him there. When his own thoughts are what's holding him back, will she be able to free him?


**Hey everyone! This fic is an OUAT Secret Santa present for _hoookedswan_ over on tumblr. So sorry it's late darling but I hope you like it!**

 **Disclaimer: Obviously, I don't own anything lol.**

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Emma's heart was weighed down by the horrors she'd seen of the Underworld so far, her hope growing dimmer by the second when finally, she saw him. The breath whooshed out of her lungs as she took in the sight of him curled tight into the corner of a cage.

"Killian," she gasped, sorrow and relief overtaking her all at once before she managed to get her body to move again.

"Killian!" She cried out, louder this time as she ran towards him. He didn't react at all, not seeming to have heard her call as he remained curled into himself in a corner.

"Killian!" She fell to her knees in front of the cage and held onto the bars. "Killian, it's me! It's gonna be okay, we're gonna get you out of here!"

"He won't answer you," said a familiar and chilling voice, and Emma whipped around to face the newcomer, instinctively placing her body in front of Killian's when she saw who had joined them.

"He won't answer, because he doesn't think it's really you," Pan said, smirking at Emma.

She gritted her teeth, not wanting to play Pan's games but knowing she needed information to be able to help Killian and escape.

"What do you mean? Why doesn't he think it's me?"

Pan grinned, seeming only too happy to explain. "Well you see, things work a little differently down here. This is Hades' domain, and he likes things done a certain way. Anyone who is down here is here because their actions in life had ill intent, or caused the death of other people. Those are the ones Hades favours. But there's a catch – if, like me, you committed crimes, killed people and have no regrets, you can walk free. Hades favours those like me. He encourages us to be proud of our villainous ways, embrace the past and revel in the Underworld's lack of rules and morals. And if we do as he says, he lets us … play."

Emma's heart sank, dreading the answer to her next question.

"And how did you 'play' with Hook? Why won't he answer me?"

Pan laughed. "It was so satisfying to do it, Emma. After everything that happened between us, I wished I could get revenge on Hook for helping you and causing my downfall. But Hades was gracious, and gave me that opportunity." He grinned, pausing for emphasis, before continuing. "He won't answer you, because I've been taking your form, and taunting him as you. Giving him hope and then tearing him down again, screaming at him all the ways he failed you, and watching as he broke down over and over again. He won't respond anymore because he doesn't believe you're really here. He thinks you're me, back to cause him more pain."

Emma felt sick. It was horrible, unconscionable. She couldn't imagine the amount of pain he must have been in. Despite her best instincts, she turned her back to Pan, focusing on Hook and trying to figure out a way to get him to hear her, believe her.

"How do I get him out?"

"Oh Emma, that's so much easier said than done. He's the only one who can get himself out of that cage. You might as well give up now." Pan cackled, before turning and walking away.

Emma took a moment to examine the cage more thoroughly. The bars were metal, reasonably thick, and had a strange pattern on them, making them look as if they had once been ropes or vines that were woven together. That shouldn't matter though. If she could find the lock, she knew she could pick it. But closer examination of the cage revealed not only no lock, but no door.

She knew Pan was right. There was only one way for Killian to get out of there, she just didn't understand how.

"Killian?" She said gently. "It's really me, I promise. It's just you and me here now. My family, our friends, we all came down here to find you and bring you home. We split up to look for you but I found you first. I promise they're all here though. We love you and we're going to take you safely back home with us, okay? Please, Killian, please just look at me. I promise it's going to be okay."

Very slowly, Killian's head lifted an inch or two, until just his eyes peeked out over his arms. Emma smiled at him, and resolved to wait patiently for him to come to her.

"It's me," she said again quietly, "it's just me, Killian."

"Emma?" Her heart broke at how timidly he said her name.

Trying unsuccessfully to swallow the lump in her throat, Emma nodded in response, hoping against hope that he would believe her.

"If you're really Emma, tell me something only she would know."

Racking her brains quickly, Emma settled on the perfect moment to remind him of. "When we went to Midas' ball in the past I introduced us as Prince Charles and Princess Leia, and when I was nervous about dancing, you told me that the only rule was to pick a partner who knows what he's doing."

At this, Killian lifted his head completely and looked at her properly. Slowly, he crawled forward until he was directly in front of her. With only the bars separating them, he examined every detail of her face, wanting to be sure. "Swan? It really is you?"

"It's me, Killian. It's okay." Emma replied, making her tone as reassuring as possible.

For a moment, Killian's face lit up with joy, before falling into a devastated expression a second later.

"Love? You shouldn't be here! Why would you come here just for me?" His tone was anguished and before Emma could form a reply things started changing. She cried out in surprise as the bars of the cage shuddered and hummed, and thin, glowing blue lines appeared and wrapped themselves around the bars. They wound down like vines before setting into the metal and making the bars slightly thicker and stronger than before.

"Killian?! What's happening?!"

"One of Hades' games, love. The cage is magical."

"So what do we do? How do we get you out?" Emma was starting to feel anxious, the grim atmosphere of the Underworld finally starting to get to her. She wanted to take Killian and her family and get out as soon as possible.

"I'm not sure that we can, love. I'm so sorry."

Killian seemed so defeated and sad, looking down and away from her, and Emma knew she had to shake him out of it in order to find a way out. She reached through the bars to place her hand gently on his cheek.

"Killian? Look at me."

She waited, stroking his cheek lightly with her thumb before he eventually met her eyes again.

"We're gonna figure this out together. Tell me how this thing works and we can find a way out. I'm not leaving you. We have a whole life to live together and I'm not giving that up for anything, understand?"

His eyes filled with tears at her words, and more of the blue vines appeared, making the bars thicker and stronger again.

"Love, there is nothing I'd like more than to have that life with you, but I can't. Hades … he plays games. He loves chaos, fear, and above all those who incite them. Everything down here is designed to turn us into villains or have us waste away in solitude."

Emma's confusion must have shown on her face because Killian took a deep breath and continued.

"Swan … the cage is built from regrets. If we embrace our bad deeds and rejoice in the pain they caused then the cage melts away and we're free. But if you can't let them go then the cage remains, and with every new regret it only grows stronger."

"So, those blue lines…"

"Aye, love. New regrets adding to the cage and making it even harder to escape."

Despair filled Emma as she finally understood the challenge ahead. Killian had done many things he regretted, and many which deserved that regret. How on Earth was she going to get him to embrace them? A tear rolled down Emma's cheek as she leaned her head against the bars, her hand intertwining with Killian's. They sat in silence for a minute, soaking in each other's presence as Emma attempted to process what she'd been told. The moment was shattered when familiar voices suddenly broke the silence.

"Killian!" Henry cried out.

"Hook! Emma!" Called Charming, and Emma turned to see the group running towards them.

"Dave? Rob? Regina…" Killian struggled to wrap his mind around the amount of people who had come for him, and Emma turned back to him just in time to see the fear take over again.

"Killian? It's okay! Don't overthink it! It's…" Emma tried to reassure him, but the bars glowed and grew stronger again.

"Swan! You shouldn't have all come here! Hades will never let you out!" His breathing started to increase as he became more distressed, his eyes flitting speedily from face to face until… "Henry? Henry came too?!"

The bars glowed again and Killian's breathing became even more rapid, veering dangerously towards a panic attack.

"Killian!" Emma reached both hands through the bars, grasping either side of his face to make him look at her and trying to ignore the tight squeeze of her arms getting through this time. "Killian! Look at me. Look at me!"

His eyes met hers again, the fear and sorrow evident in them. "Just breathe with me, Hook. It's gonna be fine, just calm down. Breathe with me, and once you've settled a bit we'll all figure out the plan together. Just slow down."

Killian struggled to steady his breathing, but after a time managed to get it close to normal. After double-checking that he was fine, Emma turned to the others to explain the workings of the cage so they could help figure out a plan.

"Well it's simple, really." Regina said, looking around expectantly before rolling her eyes at everyone's blank expressions. "He just has to reason it out until the regrets are gone!"

It was Emma's turn to roll her eyes. "And that's supposed to be easy?"

"Do you have a better plan?" Regina countered, eyebrows raised and waiting for an argument.

Emma reluctantly agreed, turning back to Killian.

"Okay, Killian. This is gonna hurt but we can do this. Just to be clear though, the bars only get stronger when new regrets appear right? Not because of remembering old ones?"

"Aye, love."

Emma settled comfortably on the ground, facing only Killian and reaching both her hands through the bars to hold onto him. Her pirate was so broken, but she knew this was necessary. "Alright. First one, let's go."

Killian clenched his teeth, looking down and away before murmuring; "I never became the man my brother wanted me to be. He despised pirates, and as soon as I lost him that's exactly what I became. He would be ashamed of me."

Emma squeezed the hand she was holding as she considered it for a moment. "Killian, from everything you've told me, the most important thing your brother taught you was to have a code and stand by it. You kept to your code by becoming a pirate and refusing to serve such a cruel and corrupt king. As a pirate, you had honour. From everything you've told me about him, I think your brother would be so proud of you sticking to that code and doing what's right, and even prouder of what a good man you've become today."

Killian looked at her, a glimmer of hope in his eyes. "Do you really think so, Swan?"

Emma smiled at him. "Definitely."

Killian smiled, and suddenly the bars began to shudder again. One of the lines began to glow, red this time, before fading away and leaving the bars slightly thinner than before.

Emma's face lit up at the sight. "Killian, look! It's working! We can do this!" He nodded, seemingly lost for words. "Quick! Tell me the next one!" Emma said, wanting to replace his regrets with hope and get them all out of there as quickly as possible.

Gradually, they worked their way through Killian's regrets, talking them through and rationalising his actions until he didn't regret them anymore. They ranged from pirate deeds, to past failings, to the fact that Emma and her family and friends were in the Underworld solely to save him. Throughout it, Emma kept up a steady stream of reassurances towards Killian, knowing it was the only way he'd be able to get through it all. At last, there was just one left. By this time, Emma's heart was aching with sorrow for her love, and all she wanted to do was bundle him up and take everybody home.

But home would have to wait, because there was just one regret left before the bars would disappear, and it seemed to be the thickest and worst of them all.

"Last one, Hook. Tell me." Emma said, giving him what she hoped was an encouraging smile.

"Swan…" he began, a look of utter desolation on his face. "I can't."

"You can!" She insisted, feeling his hand shaking and holding onto it tighter. "You can tell me anything, Killian."

"Emma, I don't want…"

Emma cut him off. "I am not leaving here without you, Killian! Just tell me what it is so we can fix it!" She cried desperately.

Tears glimmered in his eyes as he looked at her, hesitating before opening his mouth to tell her. "It's the things I said to you, Emma. That night…"

… _anger, hatred, disappointment… nothing more than a pretty blonde distraction … you'll always be an orphan…_

The unforgettable words cycled through her mind quickly, making her instinctively turn her face to the side and close her eyes to hide from him.

"Swan?"

She heard him choke out her name, but couldn't quite answer yet. First, she needed to get herself under control. It was going to be a lot harder to get Killian to stop regretting what he'd said if he saw just how hurt she was by it.

"Emma?"

She pressed her trembling lips together, hard, desperate to repress the tears that seemed to be coming full force despite her best efforts.

"I'm so sorry, darling," he said, his voice cracking with anguish as a tear finally rolled down her cheek. "I'm so sorry."

Squeezing her eyes shut as tightly as possible, Emma didn't see his hand reach forward. Ever so gently, Killian wiped her tears away, her breath hitching as he cupped her cheek in his hand and stroked it gently.

"It's okay," she stuttered out eventually. "It was the darkness talking, not you."

Killian's own tears began to fall as he marvelled at how strong and selfless his lady love truly was.

"It's not okay," he replied. "I took your deepest fears and turned them on you. I hurt you with them. It may have been the darkness speaking for me, but those were things that Killian knew, not the Dark One. It's still my fault."

Emma shook her head determinedly, finally turning back to him and lifting her watery eyes to his.

"Yes, you hurt me and yes, it's gonna take me a while to get over it, but it still wasn't your fault. I know what the darkness is like, Killian, I know it could make you say and do things you would never normally dream of."

This time it was Killian's turn to hang his head, shame coursing through him.

"But Killian, you saying all those things also made me realise just how far I've come since the person I was when we first met. It made me realise that I'm not alone and afraid anymore, and even more importantly, made me more aware of just how much I'm loved. The words were such a contrast to normal, and made me realise how much care and love you treat me with, and motivated me to find a way to get you free."

"Swan… it's a great relief to me to know those words helped you to understand how important you are in the lives and hearts of your family and I. But darling, I can't just let this go. Saying those things to you is the worst thing I've ever done in my life. Against my code, against everything I believe in, against all of the emotion and feeling I have for you. The darkness definitely took over but it was still my mouth that said those words, my eyes that looked into yours and were satisfied by the agony they found there. I will never be able to forget that look on your face and I will never be able to take it back. How can I possibly not regret it?" He asked helplessly.

"You have to!" Emma cried, the feeling of helplessness beginning to descend on her too, and desperation coming in to play. "Who else is going to remind me that those things aren't true? You told me once that you liked my walls, and that you liked being the one to break them down. I need you to do it again, Killian! I need you to realise that holding on to your regret doesn't change the past, it just keeps you imprisoned here. What's done is done and I need you to accept that so you can come home with me and build me back up. Please, Killian!"

There was a brief moment of quiet, while both of them trembled with emotion and tried to think of what to do next.

"We both were our worst selves while we were Dark Ones." Emma continued quietly, and in a steadier voice. "I think we need to forgive ourselves for what we did, because I also know neither of us blames each other. We can live a life together, a happy one, we just need to forgive ourselves so we can move on. I don't blame you at all, Killian. Not even a little bit. Please just let it go."

Emma held Killian's gaze, imploring him with her eyes to believe her, and to let this final regret go.

A tear ran down Killian's cheek and his body shuddered as it finally released the tension it had been holding. The thin remnants of the bars glowed for a moment, and then faded away into nothingness.

Emma heard gasps of relief from her family behind her and a cheer of triumph from Henry, but all she could see was Killian. Their eyes met in stunned disbelief for a moment before they both fell forward into each other, tears falling as they each wrapped the other in a tight embrace. Emma buried her face in Killian's neck, breathing him in as her shoulders shook from her cries of relief. She could feel him do the same, feel his shuddering breaths against her neck and she stroked his back, desperately trying to bring comfort.

"We're gonna be okay, Killian." She whispered to him, her heart aching with all the emotions feeling like they might burst out of it. Sorrow, relief, desperation, fear, and love above all else. A love so true and strong, that prompted her to lift her head and meet his lips ever-so-gently with hers.

The caress was short, but she felt him kiss her back, and felt a spark of hope rekindle inside her as their future was made possible again.

They finally pulled back, aware of the journey ahead of them and that the rest of the group were close by and likely watching their interaction. Emma stood and helped Killian to his feet, turning towards the group and taking his hand.

He looked down at their clasped hands, before meeting her gaze again.

"Come on, Killian. Let's go home."

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 **Thanks for reading, guys! This was not beta-ed so any mistakes are mine, but I also struggled a bit writing it so I would really love to read any feedback you all might have :) Hope you all are having wonderful days/nights xx**


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